Rhodium-catalyzed Oxidative Coupling/Cyclization of Benzamides with Alkynes via C-H Bond Cleavage

被引:245
|
作者
Mochida, Satoshi [1 ]
Umeda, Nobuyoshi [1 ]
Hirano, Koji [1 ]
Satoh, Tetsuya [1 ]
Miura, Masahiro [1 ]
机构
[1] Osaka Univ, Dept Appl Chem, Fac Engn, Suita, Osaka 5650871, Japan
关键词
INTERNAL ALKYNES; CARBOXYLIC-ACIDS; DIRECT ARYLATION; PALLADIUM; FUNCTIONALIZATION; ACTIVATION; ALKALOIDS; MULTIPLE; DERIVATIVES; COMPLEX;
D O I
10.1246/cl.2010.744
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Oxidative coupling of primary, secondary, and tertiary benzamides with internal alkynes proceeds efficiently under rhodium catalysis to selectively give the corresponding 1:1 and 1:2 coupling products, accompanied by C H and/or N-H bond cleavages. Some of the products exhibit intense fluorescence in the solid state.
引用
收藏
页码:744 / 746
页数:3
相关论文
共 50 条
  • [31] Rhodium-Catalyzed Oxidative ortho-Acylation of Benzamides with Aldehydes: Direct Functionalization of the sp2 C-H Bond
    Park, Jihye
    Park, Eonjeong
    Kim, Aejin
    Lee, Youngil
    Chi, Ki-Whan
    Kwak, Jong Hwan
    Jung, Young Hoon
    Kim, In Su
    [J]. ORGANIC LETTERS, 2011, 13 (16) : 4390 - 4393
  • [32] Diastereoselective synthesis of tetrahydropyridines via rhodium-catalyzed C-H bond activation
    Lu, Colin
    Duttwyler, Simon
    Ellman, Jonathan
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [33] Rhodium-Catalyzed Atroposelective Construction of Indoles via C-H Bond Activation
    Sun, Lincong
    Chen, Haohua
    Liu, Bingxian
    Chang, Junbiao
    Kong, Lingheng
    Wang, Fen
    Lan, Yu
    Li, Xingwei
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (15) : 8391 - 8395
  • [34] Rhodium-catalyzed hydroarylation of alkynes via tetrazole-directed C-H activation
    Chen, Bin
    Jiang, Yan
    Cheng, Jiang
    Yu, Jin-Tao
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (10) : 2901 - 2904
  • [35] Rhodium(III)-Catalyzed Redox-Neutral Coupling of α-Trifluoromethylacrylic Acid with Benzamides through Directed C-H Bond Cleavage
    Yoshimoto, Risa
    Usuki, Yoshinosuke
    Satoh, Tetsuya
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (06) : 802 - 806
  • [36] Multicomponent Synthesis of Iminocoumarins via Rhodium-Catalyzed C-H Bond Activation
    Chen, Zhan
    Jin, Shengnan
    Jiang, Wenyao
    Zhu, Feimin
    Chen, Yuqi
    Zhao, Yingwei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (16): : 11006 - 11013
  • [37] Mechanisms of Rhodium(III)-Catalyzed C-H Functionalizations of Benzamides with α,α-Difluoromethylene Alkynes
    Wu, Hongli
    Li, Xiaojie
    Tang, Xiangyang
    Feng, Chao
    Huang, Genping
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (16): : 9220 - 9230
  • [38] Rhodium-catalyzed regioselective arylation of phenylazoles and related compounds with arylboron reagents via C-H bond cleavage
    Miyamura, Sawako
    Tsurugi, Hayato
    Satoh, Tetsuya
    Miura, Masahiro
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (14) : 2438 - 2442
  • [39] Chemoselective Synthesis of Naphthylamides and Isoquinolinones via Rhodium-Catalyzed Oxidative Dehydrogenative Annulation of Benzamides with Alkynes
    Shi, Zhuangzhi
    Tang, Conghui
    Jiao, Ning
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (14-15) : 2695 - 2700
  • [40] Electricity Induced Rhodium-Catalyzed Oxidative C-H/N-H Annulation of Alkynes with Arylhydrophthalazinediones
    Sen, Partha Pratim
    Prakash, Rashmi
    Roy, Sudipta Raha
    [J]. ORGANIC LETTERS, 2022, : 4530 - 4535